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  • Title: Cascade Vinyl Radical Ipso-Cyclization Reactions and the Formation of α,β-Unsaturated-β-aryl-γ-lactams from N-Propargyl Benzamides.
    Author: Luo CH, Wang PL, Chang CC.
    Journal: J Org Chem; 2021 Nov 05; 86(21):15033-15044. PubMed ID: 34591475.
    Abstract:
    Various N-(2-bromo-allyl) benzamides were used as the starting materials to study vinyl radical cyclization reactions. The vinyl radicals underwent ipso-cyclization, fragmentation, and cyclization reactions to produce β-aryl-γ-lactams with the carbonyl group remaining intact. To further study this cascade radical reaction, vinyl radicals were generated by the addition of a tributyltin radical to alkyne moieties, followed by radical ipso-cyclization, fragmentation, cyclization, and β-scission reactions with the production of a series of α,β-unsaturated-β-aryl-γ-lactam derivatives. This new type of radical reaction was examined from the substituent effects on both the amino groups and the aryl groups. A bulky tert-butyl substituent on the amino group enhanced the formation of a Z-conformation of the benzamides and facilitated vinyl radical ipso-cyclization reactions. A synthetic method for preparing α,β-unsaturated-β-aryl-γ-lactams from N-propargyl benzamides was developed.
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